RU2224759C2 - Способ получения производных пиразоло [4,3-d]пиримидин-7-она и промежуточные соединения - Google Patents
Способ получения производных пиразоло [4,3-d]пиримидин-7-она и промежуточные соединения Download PDFInfo
- Publication number
- RU2224759C2 RU2224759C2 RU2001121162/04A RU2001121162A RU2224759C2 RU 2224759 C2 RU2224759 C2 RU 2224759C2 RU 2001121162/04 A RU2001121162/04 A RU 2001121162/04A RU 2001121162 A RU2001121162 A RU 2001121162A RU 2224759 C2 RU2224759 C2 RU 2224759C2
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- Russia
- Prior art keywords
- formula
- compound
- alcohol
- lower alkyl
- residue
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 22
- 238000000034 method Methods 0.000 title claims abstract 13
- WAJNANMQOPCIPO-UHFFFAOYSA-N pyrazolo[4,3-d]pyrimidin-7-one Chemical class O=C1N=CN=C2C=NN=C12 WAJNANMQOPCIPO-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract 7
- 230000003993 interaction Effects 0.000 claims abstract 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 4
- 230000000269 nucleophilic effect Effects 0.000 claims abstract 4
- 150000001298 alcohols Chemical class 0.000 claims abstract 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract 3
- 125000002393 azetidinyl group Chemical group 0.000 claims abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
- 239000002904 solvent Substances 0.000 claims abstract 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract 2
- 150000004703 alkoxides Chemical class 0.000 claims abstract 2
- 150000001408 amides Chemical class 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 150000004678 hydrides Chemical class 0.000 claims abstract 2
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 2
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000002585 base Substances 0.000 claims 4
- 239000003513 alkali Substances 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- -1 alkaline earth metal cation Chemical class 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical group CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 abstract 1
- 208000010228 Erectile Dysfunction Diseases 0.000 abstract 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 201000001881 impotence Diseases 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 0 **C12NC1=C(*)C=C2C(CC(C1*)=C2N*(*I)C1=C)NC2=O Chemical compound **C12NC1=C(*)C=C2C(CC(C1*)=C2N*(*I)C1=C)NC2=O 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Reproductive Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0018660A GB0018660D0 (en) | 2000-07-28 | 2000-07-28 | Pharmaceutically active compounds |
| GB0018660.1 | 2000-07-28 | ||
| GB0107526A GB0107526D0 (en) | 2001-03-26 | 2001-03-26 | Process for the preparation of pyrazolo [4,3-d] pyrimidin-7-one compounds and intermediates thereof |
| GB0107526.6 | 2001-03-26 | ||
| GB0110251.6 | 2001-04-26 | ||
| GB0110251A GB0110251D0 (en) | 2001-04-26 | 2001-04-26 | Process for the preparation of pyrazolo[4,4-d]Pyrimidin-7-one compounds and intermediates thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2001121162A RU2001121162A (ru) | 2003-07-20 |
| RU2224759C2 true RU2224759C2 (ru) | 2004-02-27 |
Family
ID=27255823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2001121162/04A RU2224759C2 (ru) | 2000-07-28 | 2001-07-27 | Способ получения производных пиразоло [4,3-d]пиримидин-7-она и промежуточные соединения |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1176147A1 (enExample) |
| JP (1) | JP2002105076A (enExample) |
| KR (1) | KR20020010102A (enExample) |
| CN (1) | CN1335317A (enExample) |
| AR (1) | AR035650A1 (enExample) |
| AU (1) | AU754962B2 (enExample) |
| BR (1) | BR0103072A (enExample) |
| CA (1) | CA2354175A1 (enExample) |
| CZ (1) | CZ20012713A3 (enExample) |
| HK (1) | HK1040715A1 (enExample) |
| HU (1) | HUP0103075A3 (enExample) |
| IL (1) | IL144516A0 (enExample) |
| IN (1) | IN191315B (enExample) |
| MX (1) | MXPA01007676A (enExample) |
| PL (1) | PL348935A1 (enExample) |
| RU (1) | RU2224759C2 (enExample) |
| YU (1) | YU51701A (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6831074B2 (en) | 2001-03-16 | 2004-12-14 | Pfizer Inc | Pharmaceutically active compounds |
| GB0106631D0 (en) * | 2001-03-16 | 2001-05-09 | Pfizer Ltd | Pharmaceutically active compounds |
| DK1620437T3 (da) | 2003-04-29 | 2009-08-24 | Pfizer Ltd | 5,7-diaminopyrazolo-4,3-d-pyrimidiner, der er anvendelige til behandling af hypertension |
| JP2006219373A (ja) | 2003-06-13 | 2006-08-24 | Daiichi Asubio Pharma Co Ltd | Pde7阻害作用を有するピリジニルピラゾロピリミジノン誘導体 |
| US7572799B2 (en) | 2003-11-24 | 2009-08-11 | Pfizer Inc | Pyrazolo[4,3-d]pyrimidines as Phosphodiesterase Inhibitors |
| ES2317209T3 (es) | 2004-04-07 | 2009-04-16 | Pfizer Inc. | Pirazolo(4,3-) pirimidinas. |
| ATE464289T1 (de) * | 2005-11-16 | 2010-04-15 | Hoffmann La Roche | Neues verfahren zur herstellung von thoc |
| WO2007107733A1 (en) * | 2006-03-17 | 2007-09-27 | Cipla Limited | Synthesis of 4-[1-(4-cyano phenyl)-(1,2,4-tr1azol-1-yl)methyl] benzonitrile and 4-[1-(1h-1,2,4-triazol-1-yl)methylene benzonitrile intermediate |
| US7638541B2 (en) | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| US8183381B2 (en) | 2007-07-19 | 2012-05-22 | Metabolex Inc. | N-linked heterocyclic receptor agonists for the treatment of diabetes and metabolic disorders |
| EP2483281B1 (en) | 2009-10-01 | 2014-06-04 | Cymabay Therapeutics, Inc. | Substituted tetrazol-1-yl-phenoxymethyl-thiazol-2-yl-piperidinyl-pyrimidine salts |
| WO2011163090A1 (en) | 2010-06-23 | 2011-12-29 | Metabolex, Inc. | Compositions of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| AU2017305392A1 (en) | 2016-08-03 | 2019-02-21 | Cymabay Therapeutics, Inc. | Oxymethylene aryl compounds for treating inflammatory gastrointestinal diseases or gastrointestinal conditions |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2114114C1 (ru) * | 1990-06-20 | 1998-06-27 | Пфайзер Инк. | Пиразолопиримидиноновые соединения, фармацевтическая композиция и способ лечения |
| RU2114113C1 (ru) * | 1991-07-09 | 1998-06-27 | Пфайзер Инк. | Пиразолопиримидиноны, фармацевтическая композиция и способ ингибирования фосфодиэстеразы циклического гуанозин-3',5'-монофосфата |
| WO2001027112A1 (en) * | 1999-10-11 | 2001-04-19 | Pfizer Limited | 5-(2-substituted-5-heterocyclylsulphonylpyrid-3-yl)-dihydropyrazolo[4,3-d]pyrimidin-7-ones as phosphodiesterase inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2089971A (en) * | 1937-08-17 | Condensation products of | ||
| GB9612514D0 (en) * | 1996-06-14 | 1996-08-14 | Pfizer Ltd | Novel process |
| GB9822238D0 (en) * | 1998-10-12 | 1998-12-09 | Pfizer Ltd | Process for preparation of pyrazolo[4,3-D]pyrimidin-7-ones and intermediates thereof |
| GB9823101D0 (en) * | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
-
2001
- 2001-07-17 YU YU51701A patent/YU51701A/sh unknown
- 2001-07-17 EP EP01306123A patent/EP1176147A1/en not_active Withdrawn
- 2001-07-20 IN IN698MU2001 patent/IN191315B/en unknown
- 2001-07-23 IL IL14451601A patent/IL144516A0/xx unknown
- 2001-07-25 CZ CZ20012713A patent/CZ20012713A3/cs unknown
- 2001-07-26 AU AU57672/01A patent/AU754962B2/en not_active Ceased
- 2001-07-26 AR ARP010103577A patent/AR035650A1/es not_active Application Discontinuation
- 2001-07-26 CA CA002354175A patent/CA2354175A1/en not_active Abandoned
- 2001-07-26 PL PL01348935A patent/PL348935A1/xx not_active Application Discontinuation
- 2001-07-27 MX MXPA01007676A patent/MXPA01007676A/es unknown
- 2001-07-27 KR KR1020010045414A patent/KR20020010102A/ko not_active Ceased
- 2001-07-27 CN CN01124351A patent/CN1335317A/zh active Pending
- 2001-07-27 RU RU2001121162/04A patent/RU2224759C2/ru not_active IP Right Cessation
- 2001-07-27 HU HU0103075A patent/HUP0103075A3/hu unknown
- 2001-07-30 BR BR0103072-8A patent/BR0103072A/pt not_active IP Right Cessation
- 2001-07-30 JP JP2001229348A patent/JP2002105076A/ja active Pending
-
2002
- 2002-04-03 HK HK02102460.5A patent/HK1040715A1/zh unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2114114C1 (ru) * | 1990-06-20 | 1998-06-27 | Пфайзер Инк. | Пиразолопиримидиноновые соединения, фармацевтическая композиция и способ лечения |
| RU2114113C1 (ru) * | 1991-07-09 | 1998-06-27 | Пфайзер Инк. | Пиразолопиримидиноны, фармацевтическая композиция и способ ингибирования фосфодиэстеразы циклического гуанозин-3',5'-монофосфата |
| WO2001027112A1 (en) * | 1999-10-11 | 2001-04-19 | Pfizer Limited | 5-(2-substituted-5-heterocyclylsulphonylpyrid-3-yl)-dihydropyrazolo[4,3-d]pyrimidin-7-ones as phosphodiesterase inhibitors |
Non-Patent Citations (2)
| Title |
|---|
| кол. 7-8. DUMAITRE В., DODIC N. Synthesis and cyclic GMP phosphodiesterase inhibitory activity of series of 6-phenylpyrasolo[3,4-d]pyrimidones. J. Med. Chem. V.39, no.8, 1996, p.1635-1644. HAMILTON H.W. et.al. Synthesis and structure-activity relationships of pyrasolo[3,4-d]pyrimidin-7-ones as adenosine reseptor antagonist. J. Med. Chem. V.30, no.1, 1987, p.91-96. * |
| кол.16-17. * |
Also Published As
| Publication number | Publication date |
|---|---|
| AR035650A1 (es) | 2004-06-23 |
| IL144516A0 (en) | 2002-05-23 |
| YU51701A (sh) | 2003-12-31 |
| JP2002105076A (ja) | 2002-04-10 |
| BR0103072A (pt) | 2002-04-09 |
| CN1335317A (zh) | 2002-02-13 |
| MXPA01007676A (es) | 2002-10-23 |
| HK1040715A1 (zh) | 2002-06-21 |
| CZ20012713A3 (cs) | 2002-04-17 |
| AU754962B2 (en) | 2002-11-28 |
| KR20020010102A (ko) | 2002-02-02 |
| HU0103075D0 (en) | 2001-10-28 |
| HUP0103075A3 (en) | 2003-04-28 |
| CA2354175A1 (en) | 2002-01-28 |
| IN191315B (enExample) | 2003-11-22 |
| EP1176147A1 (en) | 2002-01-30 |
| HUP0103075A2 (hu) | 2002-07-29 |
| PL348935A1 (en) | 2002-02-11 |
| AU5767201A (en) | 2002-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20040728 |